Hong Shen, J. Nie, Duanjun Xu
May 24, 2008
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Acta Crystallographica Section E: Structure Reports Online
Abstract
The title compound, C12H9N2 +·C7H4ClO3 −·C12H8N2·C7H5ClO3, contains one phenanthrolinium (Hphen) cation, one phenanthroline (phen) molecule, one 4-chloro-2-hydroxybenzoate anion (hcba) and one 4-chloro-2-hydroxybenzoic acid (Hhcba) molecule in the asymmetric unit. The phen molecule is approximately parallel to Hphen, making a dihedral angle of 1.98 (6)°. The centroid–centroid distance between pyridine rings of adjacent phen and Hphen species is 3.7718 (15) Å, and that between the benzene and pyridine rings of adjacent phen and Hphen species is 3.7922 (16) Å, indicative of π–π stacking interactions. The crystal structure contains an extensive network of classical (O—H⋯O, N—H⋯N and O—H⋯Cl) and weak (C—H⋯O and C—H⋯N) hydrogen bonds. Finally, C—H⋯π interactions are seen between Hphen and hcba and between phen and Hhcba in the crystal structure. The hydroxy group of the anion is disordered over the two sites ortho to the carboxylate group in a 0.75:0.25 ratio.